Chloroacetic Acid → HCID 15919477, compound

HRID 542282Notes

Reaction equation

HRID 542282 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5]1=[O:12].[Cl:13][CH2:14][C:15](O)=[O:16].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[Cl:13][CH2:14][C:15]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5]1=[O:12])=[O:16]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 159194761-(2-Hydroxyethyl)-3,4-dimethyl-1H-pyrrole-2,5-dione

Product 1

HCID 15919477HCID 15919477, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With stirring, 169.2 g (1 mole) of N-(2-hydroxyethyl)dimethylmaleimide, 113.4 g (1.2 moles) of chloroacetic acid and 11.8 g of concentrated sulfuric acid are heated to reflux in 1000 ml of toluene using a water separator. The formation of water ceases after about 2 hours and 18 ml have separated. The reaction solution is washed with saturated sodium bicarbonate solution and water. The organic phase is dried over magnesium sulfate and concentrated in a rotary evaporator at 40° C. The residue is dried for 2 hours at 60° C./0.1 mm, affording 206 g of a colourless liquid.

Workup

  1. custom18 ml have separated
  2. washThe reaction solution is washed with saturated sodium bicarbonate solution and water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator at 40° C
  5. customThe residue is dried for 2 hours at 60° C./0.1 mm

Sources & evidence

ORD record
ord-03b0dedfff4e42e580678d5362f56a7e
Source dataset
uspto-grants-1987_04
Patent number
US04656292

Reaction notes

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